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Captain Chaos, known as "Jim" to his peers, is perhaps the most knowledgeable (meta)human in the Sixth World as the SysOp of the Shadowland BBS, a shadow-resource for the underground community of Seattle, until the most recent Crash. Formerly a news network journalist, Captain Chaos was a member of the North American Neo-Anarchists before becoming SysOp and has ran Shadowland for most of its more turbulent history.

In his will, Dunkelzahn left Captain Chaos an encrypted program named "JackBNimble". Despite many attempts, Captain Chaos was never able to crack JackBNimble. He was believed to have been in his 70s during the Crash of 2064 when he "went down with his ship," dying while defending the Shadowland BBS. JackBNimble appears to have been activated by Jormungand, and subsequently "saved" a "copy" of Captain Chaos. Rumor has it that this entity is self-aware, and that it has subsequently fallen into hands of the Dunkelzahn Institute of Magical Research.

Captain Chaos' meat-body appears to have died in the Crash of 2064. FastJack appears to know the location of Captain Chaos' final resting place.